VP, Product

About Sixfold

Sixfold is building AI agents that understand risk the way a 20-year veteran underwriter does—not summaries or flags, but systems that make real decisions on billions in premium for some of the world's largest carriers. AI is the product, the workflow, and the moat.

• Product: Sixfold is the AI brain for underwriting. Our platform handles submissions at scale, assessing risk against appetite, surfacing cited insights, and deploying AI agents to handle research, referrals, and triage so underwriters can focus on building profitable portfolios.
• Team: A focused team of insurance operators, AI researchers, and engineers who love hard problems. We've pushed the boundaries of what AI can do with unstructured data—from teaching AI to understand that a bakery in Florida faces different risks than one in Montana, to knowing when a manufacturing company's pivot from toys to medical devices fundamentally changes their risk profile. We ship fast and stay close to customers.
• Traction: Processing billions in premium for some of the world's largest carriers. We know AI. We know underwriting. We're building what comes next.

About the Role

You'll inherit a strong product and a capable team, but that's the starting point, not the job. The job is figuring out what underwriting becomes once AI stops assisting and starts deciding, and getting there faster than the market expects. You prototype to find out, not to perform speed. You're drawn to this problem because the underwriter of the future is one of the most interesting design problems in software right now.

Responsibilities

• Set the direction for what AI-native underwriting looks like at Sixfold, and hold a 12-month theme even as the tactics under it change frequently.
• Build the first version of new ideas yourself: a prototype, a working demo, or a lighthouse customer test, before asking the team to build the tenth.
• Stay current enough on AI’s leading edge to have a real opinion on where things are going, not just what’s already shipped.
• Represent Sixfold's view of where underwriting is headed with customers, partners, and the industry, so people outside the company measure their own thinking against yours.
• Take ownership of the existing product and team and raise the bar on how they operate, without mistaking "it's not broken" for "it's finished."
• Partner closely with design and engineering so prototyping speed doesn't turn into technical debt. Speed and guardrails are both your job, not competing ones.

What Success Looks Like

• Within three months: You’ll have a visceral understanding of our risk-reasoning AI. If you're still relying on our current product docs instead of having your own opinion on where the edges are broken, we’ve missed the mark.
• By the end of the first quarter: Our engineering team should be moving faster, not because you managed them, but because you provided more clarity to them.

Qualifications

• You think about the underwriter of the future the way some people think about a chess position. You can't stop turning it over, and you have hot takes about what's underrated.
• When you say you built something yourself, you mean you wrote the prompt chains, ran the eval, sat with the customer—not that you wrote the spec and someone else built it.
• You took something from zero to production, and you know the ARR, retention, or adoption number it moved.
• Facing a new problem, your instinct is to build something small and get it in front of a real customer rather than write a spec. You find the lighthouse customer, get honest feedback, and iterate from there.
• You can hold a clear 12-month theme for the product. The destination doesn't move even if the path there does. You just don't confuse that with a fixed roadmap of mechanisms, since you expect to rebuild those every few months as reality changes.
• You use AI heavily in how you work, but you know the difference between AI helping you get somewhere faster and AI deciding where you end up. The taste, the risk judgment, and the call on what's worth building are still yours.
• You've inherited good teams before and know the difference between "this is broken, replace it" and "this is good, but it has to improve." You default to the latter until proven otherwise.

What we're not looking for: someone who wants to manage a team more than solve the problem; someone who can't prototype and therefore can't keep pace.

Pay

Expected salary: $245,000 - $285,000 + equity + benefits.

Schedule

About half the company works in the NYC office 3–4 days a week.

This position does not include visa sponsorship. Candidates must be authorized to work in the United States without requiring employer sponsorship.

Moments We're Proud Of

• Sixfold Named One of the 100 Most Promising AI Companies in the World
• Backed by Salesforce Ventures — Here's How It Started
• Sixfold Hit 100 Billion Tokens — Here's What That Actually Means
• How Zurich Went From Pilot to Companywide Rollout in Under a Year
• Watch Our CEO Explain Sixfold's "Holy Grail" Metric